Diisobutylamine → HCID 68448515, compound

HRID 1784317Notes

Reaction equation

HRID 1784317 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:7]=[C:8]([C:15]([CH3:20])([CH3:19])[C:16]([OH:18])=O)[CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13].C(N(C(C)C)CC)(C)C.[CH2:30]([NH:34][CH2:35][CH:36]([CH3:38])[CH3:37])[CH:31]([CH3:33])[CH3:32]>ClCCl>[Cl:5][C:6]1[CH:7]=[C:8]([C:15]([CH3:20])([CH3:19])[C:16]([N:34]([CH2:35][CH:36]([CH3:38])[CH3:37])[CH2:30][CH:31]([CH3:33])[CH3:32])=[O:18])[CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 8085DiisobutylamineHCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 68448777HCID 68448777, compound

Product 1

HCID 68448515HCID 68448515, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thionyl chloride (0.54 ml, 4 eq) is added to a solution of 2-(3-chloro-4-nitrophenyl)-2-methylpropanoic acid (500 mg) in dichloromethane (1 ml). The mixture is heated under reflux for 16 hours then cooled down to ambient temperature. The solvent is evaporated off under reduced pressure at 40° C. (co-evaporation with toluene). Diisopropylethylamine (0.42 ml, 1.2 eq) and diisobutylamine (0.36 ml, 1 eq) are successively added to a solution of the acid chloride thus obtained in dichloromethane (1 ml), cooled down to 0° C. At the end of the addition, stirring is continued for 3 hours at ambient temperature then the mixture is concentrated under reduced pressure at 40° C. The residue is dissolved in ethyl ether and the organic phase is washed successively with 1N soda, a saturated solution of sodium hydrogen carbonate, salt water then dried over Na2SO4 and concentrated under reduced pressure at 40° C. Purification by flash chromatography on silica gel (eluent:heptane/ethyl acetate 8:2 to 7:3) produces the expected compound in the form of an oil which crystallizes (0.585 g; 82% yield).

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 16 hours
  3. customThe solvent is evaporated off under reduced pressure at 40° C. (co-evaporation with toluene)
  4. temperaturecooled down to 0° C
  5. additionAt the end of the addition
  6. concentrationthe mixture is concentrated under reduced pressure at 40° C
  7. dissolutionThe residue is dissolved in ethyl ether
  8. washthe organic phase is washed successively with 1N soda
  9. dry with materiala saturated solution of sodium hydrogen carbonate, salt water then dried over Na2SO4
  10. concentrationconcentrated under reduced pressure at 40° C
  11. customPurification by flash chromatography on silica gel (eluent:heptane/ethyl acetate 8:2 to 7:3)

Sources & evidence

ORD record
ord-a67b869a08784a34a876df49a6c97e47
Source dataset
uspto-grants-2009_03
Patent number
US07501525B2

Reaction notes

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